Hydrochloric Acid → 6-Bromo-3-(di-n-propylamino)chromane

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Reaction Steps

The free base of 3-(di-n-propylamino)chromane (60 mg, 0.026 mmol) was converted to the hydrochloride with HCl-saturated EtOH. The residue after evaporation of the solvent and excess HCl was dissolved in CH2Cl2 and 4 equivalents of Br2 dissolved in CH2Cl2 were added. The reaction was complete after 2 hours and water was added. The product was found in the organic layer, which was basified with 10% Na2CO3. The organic phase was dried (Na2SO4), filtered and the solvent was evaporated, yielding an oil, which was converted to the hydrochloride with HCl-saturated EtOH. Crystals were formed from EtOAc-Hexane (30 mg) melting at 120° C. GC/MS showed M+ /M+2 at m/e=310.95(10%)/312.95(10%) and the base peak pair at m/e=282.00(100%)/284.00(97%).

Provenance & Evidence